We wanted to explore Cuba from every angle we could. To do this, we embarked towards the small countryside town of Vinales, where we stayed with a former international Cuban baseball player who played at the Olympics. His name was Orestes, and his wife Lourdes was a phenomenal cook.
We were told that Vinales’ sporting hero Orestes would be waiting for us at the bus stop. We didn’t know he was a former famous player, but when we stepped off the bus and saw an unusually tall and built Cuban man, we suspected he must have been some kind of athlete. Orestes helped us with our bags to his home, where we met his wife Lourdes, and their son’s girlfriend. Their son was away on military duty at the time, and we guessed that the girlfriend was helping them out with the family business (although that term doesn’t really apply in Cuba). Casas can only operate if licensed by the government. The Castro regime has their hand in everything, so it doesn’t matter if you’re a local farmer cultivating coffee or a former famous baseball player – everybody is essentially equal, since the government takes almost all of your earnings anyway.
Upon arrival in Vinales, we were showed the way to our spacious room which had outdoor chairs and tables. In Cuba, there are no hostels and all of the hotels are government-run. This is the only way to impact in a positive way while travelling through Cuba – trying to give what money you can to the locals who allow people to stay in their homes. The government still gets their cut. Nothing rung this home harder than when the police arrived at our home in Havana. The look on our host family’s faces was terror. As the police woman entered, books and records of who stayed and when were presented. Cash was beginning to change hands. We left that place (the best of any accommodation on our trip) with that raw reminder that the government will literally enter your home and take what they want. The implementation of a dual currency (Cuban Pesos [CUP] for locals, and Convertible Pesos [CUC] for foreigners) also means that certain shops won’t serve you unless you’re Cuban. In some places, I couldn’t even buy a bottle of water. This means that trying to leave behind extra money for the locals is worthless, since they can’t convert it, as to do so, they need to go into a government-run exchange house (and they’d be busted). Keep in mind too that one foreign peso is worth 24 local pesos, so you pay 24 times as much for everything than what locals do. Given the average price of a mojito almost everywhere is only $2, you can’t complain.

So, the reality of Cuba’s “tax” system is what made our experience with Orestes most interesting: We reasonably expected a former sports star to live somewhat lavishly, but there was no indication at all that he was better off than anyone else.
The best way to describe Vinales would be as a small, sleepy town with lots of greenery, old American cars and rugged streets. It feels smaller than most country towns we have been to, and reminds us more of a village. As soon as we arrived, Orestes and Lourdes ushered us outside to a table and two chairs and showed us a couple of activity menus we might be interested in. We asked if we could go horse riding through the countryside, and Lourdes arranged for us to leave an hour later. While we waited, she cooked us hot dogs in bread rolls with an oddly-textured cheese. It looked like tofu, but its taste was more subtle feta. Anyway, after we finished lunch inside we returned outside, where Orestes showed us newspaper clippings about him from when he was an international baseball player. He also showed us a handwritten note from Fidel Castro addressed to him, letting Orestes know that he is proud of him for representing the Cuban people at the Olympics (might have been Atlanta or Sydney, we can’t remember). It was amazing to see this handwritten note addressed to him, and he was very proud and happy to show us. Before we knew it, a local came to the front door and we were off to ride horses through some of the remotest places we’d ever been. On the way out, we noticed a huge plethora of baseball trophies Orestes had won as a professional. Lourdes informed us that he now dedicated his time to teaching children how to play.
Off we left with a young Cuban guy who couldn’t speak much English. We walked around for ages while trying to find bottled water, but everywhere was sold out – and it was extremely hot in Vinales! After conceding that we wouldn’t have any water for the next six or seven hours, we trekked through a village until we arrived at his brother’s house. Before we arrived, he asked if we spoke any Spanish at all. Repeatedly. Nope… Not anything that would allow us to converse properly, unfortunately. When we met his brother and jumped on our horses, we realised why he had sounded so disappointed when we told him no: his brother didn’t speak a word of English. Which was okay by us, but as the day wore on we couldn’t understand anything he said, so we’re sure that plenty of interesting and important facts went in one ear and out the other. For hours on end, we rode through small, rustic villages and at our first stop, we galloped up to a small barn house where a legitimate Cuban cigar roller was waiting. Inside the barn, the Cuban man asked us to sit at his wooden table. This was as farmland as you get – the only difference between the inside of the barn and the outside, was that there were four walls and a roof.

“You wanna smoke a cigar, my friend?” He asked.
“Okay,” I replied – why else was I in a Cuban tobacco farmer’s barn house?
“This is the best cigar in Cuba. I made this with my bare hands. This doesn’t have any preservatives. It’s fresh. Not like the Montecristo’s they roll in the Havana factories.”
I nodded. He had a point. He pulled out a hand-rolled cigar, chopped the butt off, and dipped the end in honey.
“This allows you to draw the smoke through without it being harsh. it also gives a good taste.” I drew on the cigar, and felt like I always felt when smoking a cigar: out of my depth. Weren’t cigars reserved for older, more hardcore folk? I was a water rat from Australia with shaggy hair and a beard. As much as I wish I did, I did not fit the picture.
As I sucked the hot smoke back through the tunnel of the cigar, it caused the thick honey to crackle and pop. The honey didn’t change the flavour of the cigar as much as one might expect, but it did help to hold in any flaky bits from the cut. It dawned on me that I was surrounded by genuine, hard-as-nails Cuban tobacco farmers, and I was sitting in a tiny barn house in a small village so far away from home that the classic backpacking concept of “Going off the beaten path” looked tired. Where ever we were wasn’t off the beaten path. It was a whole other world.
While smoking the cigar, the man who looked like a darker version of Crocodile Dundee, taught us how to roll a cigar from scratch: How to tell the difference between young and old leaves, how to add flavours to them with rum and honey, how to roll them up inside a bigger tobacco leaf and create the perfect cylinder, and how to store them so that four months from today, they would be ready to smoke! It was all eye-opening, and a much more primitive, simple yet complicated process than what I was expecting. The most interesting part was when the tobacco farmer bent the cigars in half – showing to us how flexible they were when raw. After four months in the bottom of his fridge, alongside his vegetables, they would harden up the way most smokers know them to be.
I’m no connoisseur, but after smoking the finest Cuban cigars money could buy (Montecristo, Cohiba, and Epicure No.2), the cigars this farmer rolled were far superior: Smoother, tastier, and simply more enjoyable – and this is coming from a non-smoker. We heard from other backpackers who had visited Cuba that the very best cigars didn’t come from the legendary factories, which fetch a fortune in Australia and Europe, but rather from the poor farmers in the countryside. We can definitely attest to that now.
After we left the tobacco farm, we rode to a cave where we went… caving. There were a lot of tight squeezes, plenty of bats swooping over our heads, and our young guide was friendly enough to fill us in on a bunch of facts about cave formations which went way over our heads. Out in the remote areas of Vinales, there are wild banana trees and coffee plants, so we were given a chance to try them too. Caving was an interesting exercise. We hadn’t done it before, and probably won’t again, but trying to mend your body in order to make it past back-breaking rocks in pitch black darkness was humbling. I wondered how many poor cavers got trapped, had rocks slide on top of them, or drowned from rainfall – since half way through caving, the rain started falling and the cave began flooding!
We jumped back on our horses to visit another small village. This one gave us coconuts on arrival and showed us how they farmed coffee plants and pineapples. We were genuinely intrigued by how much interesting and complicated work goes into farming, and appreciate eco-tourism a lot more now. At this farm, we mostly sat around for a while while our local guide exchanged banter for almost an hour with one of the other farmers. We were given samples of a local alcohol similar to rum, with a piece of fruit in it. A few coconut juices and mystery-rums later, Sam became fixated on the chickens, and took countless photos of them. We shared the table there with an Italian couple from Milan, who were doing a similar trek around Cuba. After we departed, we made our way back to the stables but not before I almost flung off my horse and into a fence heavy with barbed wire. The paths in the Cuban villages are treacherous: there are pot holes everywhere, uneven ground and deep ditches. Our guide decided it was a good idea to yell at my horse to run downhill through ditches and pot holes. Suicide 101 if I ever saw it. My horse absolutely stacked it, fell and seemed like it was a millimeter away from snapping all its legs. I was flung forward but managed to hold on. My horse recovered after falling over towards the barbed wire fence. The guide thought it was funny.
Once we got off our horses we noticed that the animals were branded the old school way, numbered with hot irons. That’s considered animal cruelty these days but Cuba is in a giant time warp, so we doubted they knew any differently. After we headed back to our house, Lourdes cooked up GIANT LOBSTER for us. So big, I had to finish Sam’s for her. They were larger than the plate. We didn’t realise lobster came so big. Back home, it would be well over $100 IF you could order something this size, but in the Cuban countryside (and all of Cuba, for that matter), king lobsters are normal. Commonplace, even. It’s their version of chicken. Something we would both gladly enjoy over the next three and a half weeks in Cuba.
In Vinales, the highlight of our trip was ordering a taxi to drive us an hour away to a beautiful beach called Cayo Jutias. Seriously beautiful. Remember, there are nice beaches to be found all over the world, but this was the Caribbean, which meant the water was warm, flawless, and bright blue. To make the experience better, we were driving in an old American car, with music blaring as we passed plenty of villages in the Cuban countryside. At the beach, we noticed that nobody was drinking beer. Over in Cuba, people buy bottles of rum and drink them at the beach. They even swim out into the ocean with bottles of rum and small glasses, floating around and getting drunk. We laughed on the drive there and on the way back, as it felt like a scene out of a Hollywood movie: Old American car, perfect countryside, and an even more perfect beach all chaperoned by a young, friendly Cuban guy.
We would soon get ready to leave Vinales and head to Trinidad. During our week in Vinales, we experienced a secluded Latin experience that was far from commercial or even widely known. Largely, this was attributable to it being Cuba. It may very well be one of the last places on Earth that isn’t Westernised or in some way influenced by the West. Or even modern technology. Before we departed, I bought a few books and newspapers detailing the many botched CIA missions that were sprung into action in a bid to overthrow the country. America had gone as far as poisoning everyday folk just to get back at Castro, and to wage a war. There are of course two sides to every story, and I guess what I now hold in my hands would be declared as anti-American propaganda, but from our experiences with Cubans, there are zero hostilities towards Americans. It’s just the US government they don’t like.



I did a few background checks on these alleged CIA missions which aimed to cripple Cuba’s agricultural industries, and incite terrorism, and according to Wiki Leaks and even recently released US Government files, they check out. The plot thickens… Biological and chemical weapons were used on innocent Cuban civilians. A ridiculous number of assassination attempts were made on Castro (including giving him an exploding cigar, and a wet suit filled with poisonous algae). I mean, after reading through all of this, including the accusations the US government had admitted to, it was both macabre and creative. You couldn’t even think half of this stuff up if you tried…
But as they say in Cuba:
“A lie runs until it is overtaken by the truth.”
I was looking at the legal way to go to Cuba as an American citizen but it costs so much through this tour InsightCuba. So I think I will do it on my own either “illegaly” or through my other citizenship. Would you know if they offer tours once over there? Did you just arrange all the tours you did through your casa?
Hi Boots,
There isn’t really a tourism industry at all… the horse riding tour we did, we arranged at our casa in Vinales. There are random people on the streets offering to take you to see the countryside, or to visit different beaches, but with a map it’s pretty easy to make your way there. I’d recommend taking one of the cabs, who wait for you while you’re at the beach, and don’t end up costing much at all. There is one company that I saw in Trinidad which operated a few tours to some breathtaking waterfalls and beaches, and they have an office in the main part of town.
For Havana, we took the hop-on hop-off bus to get a feel for the city, and then decided to visit the Revolution Museum. I did see one group of people who had a Cuban guide, although I didn’t see that service advertised anywhere (but I’m sure it can be found online).
The good thing about Cuba is that things are really simple for getting around: There are different areas of the city you can take the bus to visit, all of which can be organized at the local bus terminals. Just be careful not to bring US dollars with you, as they will charge you an extra 10% conversion fee, on top of the 8% they already charge. We exchanged our Aussie dollars into Euros first, but Canadian dollars are also fine.
It might be best to travel from the US on your other citizenship, or use your US passport to travel to Mexico, then your other citizenship to travel to Cuba and back to Mexico. That way, when you return from Mexico to the US, there’s no trace of you ever having left Mexico 🙂
Thanks so much. I appreciate that! I am contemplating on just going through my Filipino citizenship. To go legally from the US will cost over $6,000. Its too pricey when Cuba is so cheap. I bet you didnt even spend half of that around there? Anyway, are you doing more posts anytime soon? Really love your posts! Thanks again for answering my questions.
Hey Boots, I have a new post up now about Cuba. I’m back in Australia now, and have one more to write before moving onto Mexico… 🙂 Nope, definitely didn’t pay that much!! When do you think you would like to go??